Obscure Borgia-Related Places (4): Senigallia

  • Posted by : admin
  • 4 April 2022

Senigallia is a tiny town squeezed between its big brother Ancona towards the east, and Pesaro and Fano towards the west. Its back is protected by the gorgeous Apennines and in front, there is only blue blue sea. Today, the town is certainly ‘Italy off the beaten track’ and on its velvet beaches, you find natives only.

According to history, the Senoni Gauls, a Celtic tribe that had invaded Italy as far as the Esino river, invaded the place. Other historians claim the word ‘Sena’ derives from Etruscan tribes and the part ‘Gallia’ was added later on by the Romans. Between 290 and 280 AD, the Romans defeated Sena and it became the first Roman colony at the Adriatic Sea. In 800, Charlemagne briefly stayed in the city on his way to Rome for his coronation as emperor of the Holy Roman Empire.

However, let’s make a huge jump to the days that are more familiar to us: the Italian Renaissance. In 1474, Pope Sixtus IV, uncle of Giuliano Della Rovere (later pope Julius II), in an act of his typical nepotism, donated the vicariate of Senigallia to his nephew Giovanni Della Rovere and thus established a lordship for the Della Roveres in a fertile and prosperous part of Le Marche. In the summer of 1502, 12-year-old Francesco Della Rovere and his mother, Giovanna da Montefeltro, had to flee from the troops of Cesare Borgia who was in the process of creating a Duchy from Ancona all the way to the borders of the Papal States, Ferrara, Venice and Florence. Senigallia was now part of the Duchy that Cesare had carved out for himself. All was still quiet in the strategically placed harbor town, but in December 1502, it would forevermore become the legendary place known for the Magnificent Deceit.

At the end of September 1502, Valentino’s captains, afraid of their master’s ambition to expand his territory and dissatisfied with his rule that prevented looting in the Romagna, gathered in the castle of Cardinal Orsini in Magione and started a rebellion. Present at the secret meeting were Cardinal Orsini, old and nearly blind but still very much involved in politics, his nephew, Francesco Orsini, the unstable and naïve Paolo Orsini, Gian Paolo Baglioni and his brother Gentile and Oliverotto Uffreducci.  Vitellozzo Vitelli from Cittá di Castello who was gravely ill had to be brought in a litter to the castle. Giovanni Bentivoglio from Bologna sent his son Ermes and, Antonio da Venafro represented Pandolfo and Gentile Petrucci.[1]

Cesare was facing the rage of Italy’s most formidable and unscrupulous families. However, already there, in that very beginning of their conspiracy, not all of them were equally eager to attack the powerful Duke, to enrage the Pope and to aggravate the King of France. Although Cesare had all reason to be seriously worried, his biggest advantage in the scheme was that he was alone: sharp, secretive and lethal. As Machiavelli wrote: ‘He listens to few, decides alone and on the spur of the moment.[2]’ Being a skilled strategist himself, Cesare knew the precarious situation he was in, and he understood that with tactical skills, a decisive leader, and a good dose of courage, the rebels could have easily swept him of the map and overpower him as they commanded most parts of his own army and they knew the whereabouts of all his troops.

Like domino stones, all Cesare’s cities fell to the rebels, one after another. His troops were scattered all over the Romagna and he was forced to make haste to repost them strategically. Drunken with power and bravado, the rebel group did not stand a united front against Cesare and the crucial moment that could have led to their victory, passed. Cesare knew it and sneered at their incompetence. With every day that went by, his confidence grew, and with it his thirst for revenge.

On 19 October, Cesare showed Machiavelli the letter in which the rebels tried to seek his friendship: ‘Every day, they send me either letters or envoys to emphasize the great friendship they feel for me.[3]’ And he gloomily added: ‘But I know them!’ The acceptance of the peace treaty by Cesare initially seriously puzzled Machiavelli. He struggled to understand how it was possible that a man such as the Duke would be able to forgive the wrong that had been done to him. However, Machiavelli would soon recognise the truth behind the Duke’s façade. As Cesare had remarked earlier: ‘He would eat the artichoke leaf by leaf[4]’.

As soon as Paolo Orsini presented the draft of the Treaty to his fellow conspirators, they scoffed at it.  Unwilling to accept a status quo, Baglioni, Liverotto and Vitellozzo packed their stuff, gathered their soldiers and re-commenced their guerrilla war against Cesare[5]. Cesare did practically nothing to stop their ravaging campaigns. He bided his time and kept gathering troops who arrived from all corners of the peninsula. But, by the middle of November, it was clear that all captains were once again ready to lay down their weapons as they understood that any more banditry against the Duke’s territory and men would only fuel Cesare’s already deep resentment against them.

In Cesena, on Christmas eve, Ramiro de Lorqua was interrogated under torture and confessed his theft of grain, but much more importantly, he also unexpectedly confessed his participation in a secret conspiracy against the Duke with the Orsini, Vitellozzo and Oliverotto Uffreducci.  Cesare never mentioned a word of the conspiracy to anyone, but when he received the news that Senigallia had yielded to the rebel-condottieri, who had conquered the town in his name, and was told that the castellan, Andrea Doria only wanted to hand the keys of the rocca to the Duke, he at once became highly suspicious, and rightfully so.

On the morning of Saturday 31 December 1502, Cesare, in full armor, left from Fano with four thousand soldiers. About two kilometers from the city, Cesare met with Paolo Orsini whom he welcomed warmly with open arms. He then asked where ‘his brother’ Vitellozzo was, and the latter approached on a mule. When the Duke noticed that Liverotto was not part of all the others, he made a sign to Michelotto who went to get him, and together, they rode towards Senigallia in a happy, joyful and warm mood as if old friends finally met again.

The palace which had been prepared for the Duke was the house of Bernardino di Parma, carefully chosen by Michele da Corella for the purpose. Around nine o’clock in the evening, Cesare and his captains stopped in front of the city. Cesare asked them to enter the city and to avoid suspicion from his condotieri, he treated them with extreme friendliness and urged them to follow him. As soon as they had crossed the bridge and passed the gate, the bridge was pulled up. When they reached the house where the Duke would stay Cesare told them he would like them to go inside with him because he wanted to talk business. Surrounded by the Duke’s armed men, there was no way back. All of them entered a courtyard in the house. Then the Duke started to climb a little staircase and when he was about halfway, he turned around, rolled his eyes and at that moment, the soldiers who were in the courtyard grabbed the arms of the Duke of Gravina, Paolo Orsini, Orsino the knight, Liverotto and Vitellozzo, pulled them on their backs and pronounced them prisoners of Duca Valentino. Paolo Orsini started crying for mercy and begged Cesare to listen to him and talk.

Cesare then gave his own soldiers the order to quickly overcome the rebels’ troops. Without their leaders, most troops scattered around the country. Drunken with blood and loot, also Cesare’s soldiers began to sack the town after they had fought the Orsini and Vitello soldiers and, according to Machiavelli, it would have ended in a bloodbath if Cesare himself had not intervened on horseback, hanged some of the looters and stopped the ravage in person.

That same night, when all fighting had calmed down, Cesare decided on the fate of his prisoners. Vitellozzo and Liverotto were tortured and confessed they had been part of the conspiracy. Apparently, according to the Venetian Giustiniani, Vitellozzo confirmed what Ramiro de Lorqua had told Cesare in terms of his betrayal. After a superficial trial, the two men were garroted. The lives of the three Orsini had been spared for the moment. Cesare wanted to take them with him to Rome and imprison them together with the old Cardinal in the Rocca of Civita Castellana. But only few days later, Cesare used the garrote again when he had Paolo and Francesco killed on 18 January.

All over Italy, ‘The Magnificent Deceit’ was praised by Cesare’s contemporaries as a justifiable punishment for the rebels’ treachery, and it was called ‘the most beautiful deceit’ ever.

Unfortunately, there is no place in Italy that commemorates Cesare Borgia as the great Renaissance man he was. There are no statues of him, hardly any paintings, no buildings, universities or roads are named after him, but in the tiny sleepy town of Senigallia, there is a square, right in front of the Rocca that is called ‘La Piazza del Duca’; a quiet and respectful reference to the Duke of the Romagna. A few streets away from the Piazza del Duca, next to an elementary school, almost invisible but to those who seek for it, a modest plaque commemorates the place where the legendary Magnificent Deceit took place.


The entire plot of the Magnificent Deceit is far more complicated than told here in this short blog but the story above renders an idea of the triple betrayal of Cesare’s captains. There was simply no way Cesare would ever have been able to trust his captains again. In my book, you can read the entire story in detail.


The picture of the Rocca of Senigallia is borrowed from https://commons.wikimedia.org/wiki/File:Senigallia_-_Rocca_Roveresca_R%C3%BCckseite.JPG

The picture of the Castello di Magione is borrowed from https://it.m.wikipedia.org/wiki/File:MagioneUmbriaCastelloDeiCavalieriDiMalta2.jpg

The picture of the plaque that commemorates the Magnificent Deceit is made by SK.

The picture of the Piazza del Duca is made by SK


[1] Mallett; Clemente Fusero, The Borgias (London, Great Britain: The Pall Mall Press, 1973); Ludwig Pastor, The History of the Popes, from the Close of the Middle Ages (VI), Second Edition, I-VIII, VI (St. Louis, Missouri: B. Herder, 1902).

[2] Beuf, Cesare Borgia; The Machiavellian Prince.

[3] Sacerdote, Cesare Borgia: La sua vita, la sua famiglia, i suoi tempi.

[4] Bemis, “At the Court of the Prince: The Patronage and Art Historical Legacy of Cesare Borgia, 1492-1503”; Garner, Cesare Borgia.

[5] Fusero, The Borgias.

4 Responses

  1. I loved this story of the revenge Cesare pulled off…he did not forgive or forget …my favorite warrior in Italian history…thank you for another great post

  2. Once again, a fascinating posting. Thank you for the info and pics. You really make the times come alive again! You have a gift for making even “old” facts appear fresh by taking a new look at things.

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